#------------------------------------------------------------------------------ #$Date: 2020-04-13 14:58:09 +0300 (Mon, 13 Apr 2020) $ #$Revision: 250680 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157463.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7157463 loop_ _publ_author_name 'Ao, Chaoqun' 'Huang, Jingjing' 'Xu, Xinfang' 'Jia, Shikun' 'Kang, Zhenghui' 'Hu, Wenhao' _publ_section_title ; Rh-Catalyzed three-component reaction for the diastereoselective synthesis of pyrazolone derivatives with contiguous quaternary stereocenters ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00482K _journal_year 2020 _chemical_formula_moiety 'C31 H32 Br N3 O6' _chemical_formula_sum 'C31 H32 Br N3 O6' _chemical_formula_weight 622.50 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-12-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-16 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.2080(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.39580(10) _cell_length_b 10.3211(2) _cell_length_c 33.5425(5) _cell_measurement_reflns_used 13423 _cell_measurement_temperature 100 _cell_measurement_theta_max 75.5820 _cell_measurement_theta_min 4.4850 _cell_volume 2905.94(8) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.945 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -110.00 -24.00 0.50 0.05 -- -46.50 150.00 136.00 172 2 \w -119.00 -54.00 0.50 0.05 -- -46.50-150.00 91.00 130 3 \w -94.00 -9.00 0.50 0.05 -- -46.50 122.00 -25.00 170 4 \w -119.00 -73.00 0.50 0.05 -- -46.50-122.00-106.00 92 5 \w 13.00 94.00 0.50 0.05 -- 46.50-122.00-106.00 162 6 \w -114.00 -27.00 0.50 0.20 -- -100.00 122.00 -25.00 174 7 \w -171.00 -58.00 0.50 0.20 -- -100.00-150.00 91.00 226 8 \w -103.00 -45.00 0.50 0.20 -- -100.00 150.00 136.00 116 9 \w -172.00 -74.00 0.50 0.20 -- -100.00-122.00-106.00 196 10 \w 74.00 103.00 0.50 0.20 -- 107.00-122.00-106.00 58 11 \w 90.00 115.00 0.50 0.20 -- 107.00 150.00 136.00 50 12 \w -115.00 -73.00 0.50 0.05 -- -46.50-125.00 0.00 84 13 \w -119.00 -24.00 0.50 0.05 -- -46.50 -77.00-120.00 190 14 \w 45.00 115.00 0.50 0.05 -- 46.50 38.00 -90.00 140 15 \w -77.00 -28.00 0.50 0.20 -- -100.00 61.00-180.00 98 16 \w -172.00 -82.00 0.50 0.20 -- -100.00 -94.00 0.00 180 17 \w -116.00 -91.00 0.50 0.20 -- -100.00 61.00-180.00 50 18 \w -159.00 -77.00 0.50 0.20 -- -100.00 -77.00-180.00 164 19 \w 35.00 107.00 0.50 0.20 -- 107.00 -94.00 90.00 144 20 \w 140.00 178.00 0.50 0.20 -- 107.00 30.00 -30.00 76 21 \w 35.00 109.00 0.50 0.20 -- 107.00 -94.00 -90.00 148 22 \w 95.00 136.00 0.50 0.20 -- 107.00 30.00 -30.00 82 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0466904000 _diffrn_orient_matrix_UB_12 -0.0597237000 _diffrn_orient_matrix_UB_13 0.0406711000 _diffrn_orient_matrix_UB_21 0.0394280000 _diffrn_orient_matrix_UB_22 0.1360581000 _diffrn_orient_matrix_UB_23 0.0163703000 _diffrn_orient_matrix_UB_31 -0.1731078000 _diffrn_orient_matrix_UB_32 0.0149149000 _diffrn_orient_matrix_UB_33 0.0136119000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.945 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 27965 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.945 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.990 _diffrn_reflns_theta_min 2.635 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.333 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.59215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_description block _exptl_crystal_F_000 1288 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 1.891 _refine_diff_density_min -1.019 _refine_diff_density_rms 0.103 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 375 _refine_ls_number_reflns 5797 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0647 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0324P)^2^+15.6780P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1481 _refine_ls_wR_factor_ref 0.1546 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5194 _reflns_number_total 5797 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00482k2.cif _cod_data_source_block caiju_082_181115_2 _cod_database_code 7157463 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.800 _shelx_estimated_absorpt_t_min 0.541 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C00W(H00D,H00F) 2.b Aromatic/amide H refined with riding coordinates: N009(H009), C00E(H00E), C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011), C013(H013) 2.c Idealised Me refined as rotating group: C00T(H00A,H00B,H00C), C010(H01A,H01B,H01C), C012(H01D,H01E,H01F), C014(H01G, H01H,H01I), C015(H01J,H01K,H01L) ; _shelx_res_file ; TITL caiju_082_181115_2_a.res in P2(1)/n caiju_082_181115_2.res created by SHELXL-2016/6 at 15:08:19 on 11-Dec-2018 REM Old TITL caiju_082_181115_2 in P2(1) REM SHELXT solution in P2(1)/n REM R1 0.181, Rweak 0.112, Alpha 0.033, Orientation as input REM Formula found by SHELXT: C31 N3 O6 Br CELL 1.54184 8.3958 10.3211 33.5425 90 91.208 90 ZERR 4 0.0001 0.0002 0.0005 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Br UNIT 124 128 12 24 4 L.S. 50 PLAN 50 SIZE 0.3 0.2 0.1 TEMP -173.15 BOND $H list 4 conf htab conf fmap 2 acta REM REM REM WGHT 0.032400 15.678000 FVAR 0.30705 BR01 5 0.701789 1.197055 0.699470 11.00000 0.03690 0.02392 = 0.05241 -0.01038 0.00391 0.00066 O002 4 0.871380 0.656648 0.589525 11.00000 0.01532 0.02375 = 0.02911 -0.00104 0.00211 -0.00158 O003 4 0.569439 0.530373 0.688203 11.00000 0.02029 0.02433 = 0.03609 0.00347 0.00426 0.00056 O004 4 0.498204 0.287471 0.589338 11.00000 0.01792 0.02041 = 0.04886 -0.00583 0.00007 -0.00225 O005 4 0.954881 0.574937 0.686118 11.00000 0.02420 0.02358 = 0.03616 0.00070 -0.00392 0.00266 O006 4 0.353939 0.465074 0.607305 11.00000 0.01436 0.02169 = 0.05642 -0.00373 0.00382 0.00099 O007 4 0.918487 0.434023 0.635794 11.00000 0.02381 0.02221 = 0.04236 -0.00051 -0.00008 0.00369 N008 3 0.438827 0.705351 0.657618 11.00000 0.01614 0.02286 = 0.03172 -0.00174 0.00411 -0.00170 N009 3 0.622331 0.473670 0.601907 11.00000 0.01578 0.02166 = 0.03658 -0.00572 0.00581 -0.00229 AFIX 43 H009 2 0.708581 0.437761 0.592345 11.00000 -1.20000 AFIX 0 N00A 3 0.429025 0.758953 0.619098 11.00000 0.01868 0.02003 = 0.03275 0.00049 0.00321 -0.00259 C00B 1 0.541971 0.602547 0.660247 11.00000 0.01515 0.01887 = 0.03216 -0.00221 0.00254 -0.00357 C00C 1 0.339200 0.756736 0.687407 11.00000 0.01250 0.01952 = 0.04024 -0.00682 0.00544 -0.00274 C00D 1 0.531564 0.701731 0.597084 11.00000 0.01202 0.02135 = 0.03327 -0.00198 0.00291 -0.00078 C00E 1 0.332809 0.701201 0.724709 11.00000 0.02535 0.02430 = 0.03514 -0.00081 0.00560 0.00294 AFIX 43 H00E 2 0.398704 0.629199 0.731331 11.00000 -1.20000 AFIX 0 C00F 1 0.627569 0.600349 0.620019 11.00000 0.01733 0.01957 = 0.03126 -0.00115 0.00336 -0.00002 C00G 1 0.748148 1.028132 0.679045 11.00000 0.02127 0.02306 = 0.04114 -0.00593 0.00091 0.00136 C00H 1 0.478835 0.411349 0.600110 11.00000 0.01803 0.01807 = 0.03723 -0.00092 0.00026 -0.00171 C00I 1 0.804427 0.649163 0.627993 11.00000 0.01770 0.01955 = 0.03158 0.00005 0.00344 -0.00083 C00J 1 0.897225 0.539466 0.650776 11.00000 0.01439 0.02485 = 0.03504 0.00201 0.00377 0.00047 C00K 1 0.785150 1.016272 0.639615 11.00000 0.02147 0.01962 = 0.04098 0.00152 -0.00219 0.00012 AFIX 43 H00K 2 0.794521 1.090731 0.623180 11.00000 -1.20000 AFIX 0 C00L 1 0.797385 0.782784 0.648181 11.00000 0.01425 0.01905 = 0.03399 -0.00140 0.00173 -0.00019 C00M 1 0.808690 0.892786 0.624182 11.00000 0.02102 0.02263 = 0.03174 0.00096 0.00190 -0.00320 AFIX 43 H00M 2 0.832907 0.883138 0.596803 11.00000 -1.20000 AFIX 0 C00N 1 0.765124 0.799578 0.688194 11.00000 0.02145 0.02299 = 0.03527 0.00111 0.00072 -0.00492 AFIX 43 H00N 2 0.761310 0.726124 0.705214 11.00000 -1.20000 AFIX 0 C00O 1 1.092536 0.711542 0.549133 11.00000 0.01243 0.02915 = 0.03447 -0.00152 0.00190 0.00115 C00P 1 0.738330 0.921839 0.703783 11.00000 0.02114 0.02497 = 0.03579 -0.00299 0.00241 -0.00158 AFIX 43 H00P 2 0.713571 0.932254 0.731102 11.00000 -1.20000 AFIX 0 C00Q 1 0.247758 0.866127 0.678420 11.00000 0.01825 0.02551 = 0.03940 -0.00385 0.00280 0.00225 AFIX 43 H00Q 2 0.254988 0.906623 0.653088 11.00000 -1.20000 AFIX 0 C00R 1 0.135459 0.858109 0.743653 11.00000 0.01874 0.03162 = 0.04511 -0.01238 0.00847 -0.00482 AFIX 43 H00R 2 0.064480 0.891529 0.762795 11.00000 -1.20000 AFIX 0 C00S 1 0.229146 0.751397 0.752573 11.00000 0.02717 0.02678 = 0.03762 -0.00396 0.00965 -0.00456 AFIX 43 H00S 2 0.222621 0.711859 0.778063 11.00000 -1.20000 AFIX 0 C00T 1 0.542150 0.727075 0.553951 11.00000 0.02040 0.02705 = 0.03529 -0.00199 -0.00058 0.00186 AFIX 137 H00A 2 0.524981 0.646164 0.539187 11.00000 -1.50000 H00B 2 0.647893 0.761585 0.548135 11.00000 -1.50000 H00C 2 0.460611 0.790318 0.545869 11.00000 -1.50000 AFIX 0 C00U 1 1.104343 0.839771 0.536846 11.00000 0.02140 0.02296 = 0.04184 -0.00089 0.00294 -0.00079 AFIX 43 H00U 2 1.078557 0.907675 0.554708 11.00000 -1.20000 AFIX 0 C00V 1 0.357612 0.201894 0.585053 11.00000 0.02050 0.02049 = 0.04713 0.00025 -0.00264 -0.00759 C00W 1 1.043784 0.677319 0.590387 11.00000 0.01142 0.02766 = 0.03868 -0.00079 0.00053 -0.00200 AFIX 23 H00D 2 1.099307 0.597627 0.599442 11.00000 -1.20000 H00F 2 1.072022 0.748379 0.609059 11.00000 -1.20000 AFIX 0 C00X 1 0.146063 0.915347 0.706808 11.00000 0.02084 0.02891 = 0.04533 -0.00999 0.00091 0.00303 AFIX 43 H00X 2 0.083067 0.989468 0.700690 11.00000 -1.20000 AFIX 0 C00Y 1 1.130421 0.614397 0.522382 11.00000 0.02892 0.02833 = 0.03968 0.00145 0.00465 0.00044 AFIX 43 H00Y 2 1.123352 0.526291 0.530348 11.00000 -1.20000 AFIX 0 C00Z 1 1.191870 0.772086 0.472853 11.00000 0.02043 0.04232 = 0.03581 0.00838 0.00485 0.00073 AFIX 43 H00Z 2 1.227957 0.792728 0.446962 11.00000 -1.20000 AFIX 0 C010 1 1.048467 0.475162 0.706431 11.00000 0.02853 0.02924 = 0.04412 0.00619 -0.00627 0.00118 AFIX 137 H01A 2 1.148502 0.462031 0.692447 11.00000 -1.50000 H01B 2 0.988038 0.393934 0.706592 11.00000 -1.50000 H01C 2 1.071857 0.502358 0.733928 11.00000 -1.50000 AFIX 0 C011 1 1.153596 0.869263 0.498622 11.00000 0.02151 0.03344 = 0.04772 0.01021 -0.00022 -0.00047 AFIX 43 H011 2 1.160684 0.957100 0.490382 11.00000 -1.20000 AFIX 0 C012 1 0.431763 0.075712 0.571586 11.00000 0.02675 0.02084 = 0.08418 -0.01109 -0.00610 -0.00264 AFIX 137 H01D 2 0.480965 0.088382 0.545639 11.00000 -1.50000 H01E 2 0.349098 0.008952 0.569232 11.00000 -1.50000 H01F 2 0.513148 0.048257 0.591185 11.00000 -1.50000 AFIX 0 C013 1 1.178375 0.644135 0.484245 11.00000 0.03560 0.04145 = 0.03908 -0.00442 0.00426 0.00779 AFIX 43 H013 2 1.201905 0.576783 0.465985 11.00000 -1.20000 AFIX 0 C014 1 0.243695 0.254008 0.553273 11.00000 0.03458 0.03036 = 0.05887 -0.00059 -0.01389 -0.00307 AFIX 137 H01G 2 0.189304 0.330806 0.563471 11.00000 -1.50000 H01H 2 0.164762 0.187408 0.546263 11.00000 -1.50000 H01I 2 0.303365 0.277505 0.529539 11.00000 -1.50000 AFIX 0 C015 1 0.279784 0.185802 0.625021 11.00000 0.04357 0.03011 = 0.05667 0.00542 0.00801 -0.00760 AFIX 137 H01J 2 0.361063 0.163912 0.645313 11.00000 -1.50000 H01K 2 0.200616 0.116144 0.623298 11.00000 -1.50000 H01L 2 0.227259 0.266925 0.632343 11.00000 -1.50000 AFIX 0 HKLF 4 REM caiju_082_181115_2_a.res in P2(1)/n REM R1 = 0.0647 for 5194 Fo > 4sig(Fo) and 0.0704 for all 5797 data REM 375 parameters refined using 0 restraints END WGHT 0.0321 15.6951 REM Instructions for potential hydrogen bonds HTAB N009 O007 HTAB C00E O003 HTAB C00T O002 EQIV $1 x+1, y, z HTAB C00W O006_$1 HTAB C00W O007 HTAB C014 O006 HTAB C015 O006 REM Highest difference peak 1.891, deepest hole -1.019, 1-sigma level 0.103 Q1 1 0.7012 1.1949 0.7329 11.00000 0.05 1.89 Q2 1 0.7008 1.1905 0.6681 11.00000 0.05 1.81 Q3 1 0.7046 1.3046 0.6987 11.00000 0.05 0.75 Q4 1 0.8345 1.2320 0.6891 11.00000 0.05 0.55 Q5 1 0.6904 1.0904 0.6985 11.00000 0.05 0.53 Q6 1 0.7112 0.4219 0.6116 11.00000 0.05 0.49 Q7 1 0.8199 1.1430 0.6783 11.00000 0.05 0.48 Q8 1 0.5877 1.1440 0.7191 11.00000 0.05 0.44 Q9 1 0.5782 1.2429 0.7187 11.00000 0.05 0.43 Q10 1 0.6050 0.6599 0.6036 11.00000 0.05 0.42 Q11 1 0.6585 0.4585 0.6685 11.00000 0.05 0.41 Q12 1 0.6239 0.4627 0.6317 11.00000 0.05 0.40 Q13 1 0.3224 0.6874 0.6922 11.00000 0.05 0.40 Q14 1 0.6027 0.4711 0.5727 11.00000 0.05 0.39 Q15 1 0.3643 0.4764 0.6388 11.00000 0.05 0.39 Q16 1 0.8715 0.6628 0.6168 11.00000 0.05 0.38 Q17 1 0.9197 0.4084 0.6632 11.00000 0.05 0.37 Q18 1 0.8020 0.6904 0.7355 11.00000 0.05 0.37 Q19 1 0.8456 0.5998 0.6378 11.00000 0.05 0.37 Q20 1 0.5438 0.7374 0.5790 11.00000 0.05 0.37 Q21 1 1.0923 0.7019 0.5201 11.00000 0.05 0.37 Q22 1 0.7985 0.7776 0.6131 11.00000 0.05 0.36 Q23 1 0.2154 0.7352 0.7260 11.00000 0.05 0.36 Q24 1 0.5469 0.7346 0.5199 11.00000 0.05 0.36 Q25 1 0.6244 0.6018 0.6474 11.00000 0.05 0.36 Q26 1 0.1407 0.8378 0.7043 11.00000 0.05 0.36 Q27 1 1.1528 0.8339 0.4755 11.00000 0.05 0.36 Q28 1 1.1232 0.8351 0.5134 11.00000 0.05 0.36 Q29 1 0.3583 0.4660 0.5733 11.00000 0.05 0.35 Q30 1 0.7395 1.0052 0.7081 11.00000 0.05 0.34 Q31 1 0.6879 0.7177 0.7476 11.00000 0.05 0.34 Q32 1 0.9034 0.4154 0.6088 11.00000 0.05 0.33 Q33 1 0.4213 0.7639 0.5868 11.00000 0.05 0.33 Q34 1 0.7982 0.9001 0.5931 11.00000 0.05 0.33 Q35 1 0.4539 0.7025 0.6089 11.00000 0.05 0.33 Q36 1 0.3601 0.7086 0.6614 11.00000 0.05 0.33 Q37 1 0.7837 1.0139 0.6618 11.00000 0.05 0.33 Q38 1 0.4221 0.7390 0.6828 11.00000 0.05 0.32 Q39 1 0.7560 1.0971 0.6784 11.00000 0.05 0.32 Q40 1 0.9492 0.5477 0.7631 11.00000 0.05 0.32 Q41 1 0.3453 0.7615 0.7155 11.00000 0.05 0.31 Q42 1 0.7368 0.8037 0.6637 11.00000 0.05 0.31 Q43 1 0.8385 0.8014 0.7443 11.00000 0.05 0.31 Q44 1 0.4373 0.7308 0.6413 11.00000 0.05 0.31 Q45 1 0.8348 1.2201 0.7293 11.00000 0.05 0.31 Q46 1 0.6291 0.6612 0.5436 11.00000 0.05 0.31 Q47 1 0.3119 0.0815 0.6325 11.00000 0.05 0.31 Q48 1 1.2090 0.7735 0.4982 11.00000 0.05 0.30 Q49 1 0.5595 0.4477 0.6012 11.00000 0.05 0.30 Q50 1 0.6087 0.5736 0.5898 11.00000 0.05 0.30 ; _shelx_res_checksum 76407 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.483 _oxdiff_exptl_absorpt_empirical_full_min 0.647 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br01 Br 0.70179(6) 1.19706(5) 0.69947(2) 0.03771(16) Uani 1 1 d . . . . . O002 O 0.8714(3) 0.6566(3) 0.58952(8) 0.0227(6) Uani 1 1 d . . . . . O003 O 0.5694(3) 0.5304(3) 0.68820(8) 0.0269(6) Uani 1 1 d . . . . . O004 O 0.4982(3) 0.2875(3) 0.58934(9) 0.0291(6) Uani 1 1 d . . . . . O005 O 0.9549(3) 0.5749(3) 0.68612(9) 0.0280(6) Uani 1 1 d . . . . . O006 O 0.3539(3) 0.4651(3) 0.60731(10) 0.0308(7) Uani 1 1 d . . . . . O007 O 0.9185(3) 0.4340(3) 0.63579(9) 0.0295(6) Uani 1 1 d . . . . . N008 N 0.4388(4) 0.7054(3) 0.65762(10) 0.0235(7) Uani 1 1 d . . . . . N009 N 0.6223(4) 0.4737(3) 0.60191(10) 0.0246(7) Uani 1 1 d . . . . . H009 H 0.708581 0.437761 0.592345 0.030 Uiso 1 1 calc R . . . . N00A N 0.4290(4) 0.7590(3) 0.61910(10) 0.0238(7) Uani 1 1 d . . . . . C00B C 0.5420(4) 0.6025(4) 0.66025(12) 0.0220(8) Uani 1 1 d . . . . . C00C C 0.3392(4) 0.7567(4) 0.68741(12) 0.0240(8) Uani 1 1 d . . . . . C00D C 0.5316(4) 0.7017(4) 0.59708(12) 0.0222(8) Uani 1 1 d . . . . . C00E C 0.3328(5) 0.7012(4) 0.72471(13) 0.0282(9) Uani 1 1 d . . . . . H00E H 0.398704 0.629199 0.731331 0.034 Uiso 1 1 calc R . . . . C00F C 0.6276(4) 0.6003(4) 0.62002(12) 0.0227(8) Uani 1 1 d . . . . . C00G C 0.7481(5) 1.0281(4) 0.67904(13) 0.0285(9) Uani 1 1 d . . . . . C00H C 0.4788(4) 0.4113(4) 0.60011(12) 0.0244(8) Uani 1 1 d . . . . . C00I C 0.8044(4) 0.6492(4) 0.62799(12) 0.0229(8) Uani 1 1 d . . . . . C00J C 0.8972(4) 0.5395(4) 0.65078(12) 0.0247(8) Uani 1 1 d . . . . . C00K C 0.7851(5) 1.0163(4) 0.63961(13) 0.0274(9) Uani 1 1 d . . . . . H00K H 0.794521 1.090731 0.623180 0.033 Uiso 1 1 calc R . . . . C00L C 0.7974(4) 0.7828(4) 0.64818(12) 0.0224(8) Uani 1 1 d . . . . . C00M C 0.8087(4) 0.8928(4) 0.62418(12) 0.0251(8) Uani 1 1 d . . . . . H00M H 0.832907 0.883138 0.596803 0.030 Uiso 1 1 calc R . . . . C00N C 0.7651(5) 0.7996(4) 0.68819(13) 0.0266(8) Uani 1 1 d . . . . . H00N H 0.761310 0.726124 0.705214 0.032 Uiso 1 1 calc R . . . . C00O C 1.0925(4) 0.7115(4) 0.54913(12) 0.0253(8) Uani 1 1 d . . . . . C00P C 0.7383(5) 0.9218(4) 0.70378(13) 0.0273(8) Uani 1 1 d . . . . . H00P H 0.713571 0.932254 0.731102 0.033 Uiso 1 1 calc R . . . . C00Q C 0.2478(4) 0.8661(4) 0.67842(13) 0.0277(9) Uani 1 1 d . . . . . H00Q H 0.254988 0.906623 0.653088 0.033 Uiso 1 1 calc R . . . . C00R C 0.1355(5) 0.8581(4) 0.74365(14) 0.0317(9) Uani 1 1 d . . . . . H00R H 0.064480 0.891529 0.762795 0.038 Uiso 1 1 calc R . . . . C00S C 0.2291(5) 0.7514(4) 0.75257(14) 0.0304(9) Uani 1 1 d . . . . . H00S H 0.222621 0.711859 0.778063 0.036 Uiso 1 1 calc R . . . . C00T C 0.5421(5) 0.7271(4) 0.55395(12) 0.0276(8) Uani 1 1 d . . . . . H00A H 0.524981 0.646164 0.539187 0.041 Uiso 1 1 calc GR . . . . H00B H 0.647893 0.761585 0.548135 0.041 Uiso 1 1 calc GR . . . . H00C H 0.460611 0.790318 0.545869 0.041 Uiso 1 1 calc GR . . . . C00U C 1.1043(5) 0.8398(4) 0.53685(13) 0.0287(9) Uani 1 1 d . . . . . H00U H 1.078557 0.907675 0.554708 0.034 Uiso 1 1 calc R . . . . C00V C 0.3576(5) 0.2019(4) 0.58505(14) 0.0294(9) Uani 1 1 d . . . . . C00W C 1.0438(4) 0.6773(4) 0.59039(12) 0.0259(8) Uani 1 1 d . . . . . H00D H 1.099307 0.597627 0.599442 0.031 Uiso 1 1 calc R . . . . H00F H 1.072022 0.748379 0.609059 0.031 Uiso 1 1 calc R . . . . C00X C 0.1461(5) 0.9153(4) 0.70681(14) 0.0317(9) Uani 1 1 d . . . . . H00X H 0.083067 0.989468 0.700690 0.038 Uiso 1 1 calc R . . . . C00Y C 1.1304(5) 0.6144(4) 0.52238(13) 0.0323(9) Uani 1 1 d . . . . . H00Y H 1.123352 0.526291 0.530348 0.039 Uiso 1 1 calc R . . . . C00Z C 1.1919(5) 0.7721(5) 0.47285(13) 0.0328(10) Uani 1 1 d . . . . . H00Z H 1.227957 0.792728 0.446962 0.039 Uiso 1 1 calc R . . . . C010 C 1.0485(5) 0.4752(4) 0.70643(14) 0.0341(10) Uani 1 1 d . . . . . H01A H 1.148502 0.462031 0.692447 0.051 Uiso 1 1 calc GR . . . . H01B H 0.988038 0.393934 0.706592 0.051 Uiso 1 1 calc GR . . . . H01C H 1.071857 0.502358 0.733928 0.051 Uiso 1 1 calc GR . . . . C011 C 1.1536(5) 0.8693(5) 0.49862(14) 0.0342(10) Uani 1 1 d . . . . . H011 H 1.160684 0.957100 0.490382 0.041 Uiso 1 1 calc R . . . . C012 C 0.4318(5) 0.0757(4) 0.57159(18) 0.0440(12) Uani 1 1 d . . . . . H01D H 0.480965 0.088382 0.545639 0.066 Uiso 1 1 calc GR . . . . H01E H 0.349098 0.008952 0.569232 0.066 Uiso 1 1 calc GR . . . . H01F H 0.513148 0.048257 0.591185 0.066 Uiso 1 1 calc GR . . . . C013 C 1.1784(6) 0.6441(5) 0.48425(14) 0.0387(11) Uani 1 1 d . . . . . H013 H 1.201905 0.576783 0.465985 0.046 Uiso 1 1 calc R . . . . C014 C 0.2437(6) 0.2540(5) 0.55327(16) 0.0415(11) Uani 1 1 d . . . . . H01G H 0.189304 0.330806 0.563471 0.062 Uiso 1 1 calc GR . . . . H01H H 0.164762 0.187408 0.546263 0.062 Uiso 1 1 calc GR . . . . H01I H 0.303365 0.277505 0.529539 0.062 Uiso 1 1 calc GR . . . . C015 C 0.2798(6) 0.1858(5) 0.62502(16) 0.0434(12) Uani 1 1 d . . . . . H01J H 0.361063 0.163912 0.645313 0.065 Uiso 1 1 calc GR . . . . H01K H 0.200616 0.116144 0.623298 0.065 Uiso 1 1 calc GR . . . . H01L H 0.227259 0.266925 0.632343 0.065 Uiso 1 1 calc GR . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br01 0.0369(3) 0.0239(2) 0.0524(3) -0.0104(2) 0.0039(2) 0.00066(19) O002 0.0153(12) 0.0237(14) 0.0291(14) -0.0010(11) 0.0021(10) -0.0016(10) O003 0.0203(13) 0.0243(15) 0.0361(15) 0.0035(12) 0.0043(11) 0.0006(11) O004 0.0179(13) 0.0204(14) 0.0489(18) -0.0058(12) 0.0001(12) -0.0022(11) O005 0.0242(14) 0.0236(15) 0.0362(16) 0.0007(12) -0.0039(11) 0.0027(11) O006 0.0144(13) 0.0217(14) 0.0564(19) -0.0037(13) 0.0038(12) 0.0010(11) O007 0.0238(14) 0.0222(15) 0.0424(17) -0.0005(12) -0.0001(12) 0.0037(11) N008 0.0161(14) 0.0229(17) 0.0317(17) -0.0017(13) 0.0041(12) -0.0017(13) N009 0.0158(15) 0.0217(17) 0.0366(18) -0.0057(14) 0.0058(13) -0.0023(13) N00A 0.0187(15) 0.0200(16) 0.0327(18) 0.0005(13) 0.0032(13) -0.0026(13) C00B 0.0152(17) 0.0189(18) 0.032(2) -0.0022(16) 0.0025(14) -0.0036(14) C00C 0.0125(16) 0.0195(19) 0.040(2) -0.0068(16) 0.0054(15) -0.0027(14) C00D 0.0120(16) 0.0213(19) 0.033(2) -0.0020(16) 0.0029(14) -0.0008(14) C00E 0.025(2) 0.024(2) 0.035(2) -0.0008(17) 0.0056(16) 0.0029(16) C00F 0.0173(17) 0.0196(19) 0.031(2) -0.0012(15) 0.0034(14) 0.0000(14) C00G 0.0213(19) 0.023(2) 0.041(2) -0.0059(17) 0.0009(16) 0.0014(16) C00H 0.0180(18) 0.0181(19) 0.037(2) -0.0009(16) 0.0003(15) -0.0017(15) C00I 0.0177(17) 0.0195(19) 0.032(2) 0.0000(15) 0.0034(14) -0.0008(14) C00J 0.0144(17) 0.025(2) 0.035(2) 0.0020(17) 0.0038(15) 0.0005(15) C00K 0.0215(19) 0.0196(19) 0.041(2) 0.0015(17) -0.0022(16) 0.0001(15) C00L 0.0143(16) 0.0191(19) 0.034(2) -0.0014(15) 0.0017(14) -0.0002(14) C00M 0.0210(18) 0.023(2) 0.032(2) 0.0010(16) 0.0019(15) -0.0032(15) C00N 0.0214(18) 0.023(2) 0.035(2) 0.0011(16) 0.0007(15) -0.0049(16) C00O 0.0124(16) 0.029(2) 0.034(2) -0.0015(17) 0.0019(14) 0.0011(15) C00P 0.0211(19) 0.025(2) 0.036(2) -0.0030(17) 0.0024(16) -0.0016(16) C00Q 0.0182(18) 0.026(2) 0.039(2) -0.0039(17) 0.0028(16) 0.0023(16) C00R 0.0187(18) 0.032(2) 0.045(2) -0.0124(19) 0.0085(17) -0.0048(17) C00S 0.027(2) 0.027(2) 0.038(2) -0.0040(18) 0.0097(17) -0.0046(17) C00T 0.0204(18) 0.027(2) 0.035(2) -0.0020(17) -0.0006(15) 0.0019(16) C00U 0.0214(19) 0.023(2) 0.042(2) -0.0009(17) 0.0029(16) -0.0008(16) C00V 0.0205(19) 0.020(2) 0.047(2) 0.0003(18) -0.0026(17) -0.0076(16) C00W 0.0114(16) 0.028(2) 0.039(2) -0.0008(17) 0.0005(14) -0.0020(15) C00X 0.0208(19) 0.029(2) 0.045(3) -0.0100(19) 0.0009(17) 0.0030(17) C00Y 0.029(2) 0.028(2) 0.040(2) 0.0014(18) 0.0046(17) 0.0004(18) C00Z 0.0204(19) 0.042(3) 0.036(2) 0.008(2) 0.0048(16) 0.0007(18) C010 0.029(2) 0.029(2) 0.044(3) 0.0062(19) -0.0063(18) 0.0012(18) C011 0.022(2) 0.033(2) 0.048(3) 0.010(2) -0.0002(18) -0.0005(18) C012 0.027(2) 0.021(2) 0.084(4) -0.011(2) -0.006(2) -0.0026(18) C013 0.036(2) 0.041(3) 0.039(2) -0.004(2) 0.0043(19) 0.008(2) C014 0.035(2) 0.030(2) 0.059(3) -0.001(2) -0.014(2) -0.003(2) C015 0.044(3) 0.030(3) 0.057(3) 0.005(2) 0.008(2) -0.008(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00I O002 C00W 113.6(3) . . ? C00H O004 C00V 119.7(3) . . ? C00J O005 C010 114.0(3) . . ? N00A N008 C00C 118.4(3) . . ? C00B N008 N00A 112.8(3) . . ? C00B N008 C00C 128.7(3) . . ? C00F N009 H009 121.2 . . ? C00H N009 H009 121.2 . . ? C00H N009 C00F 117.7(3) . . ? C00D N00A N008 108.6(3) . . ? O003 C00B N008 129.3(4) . . ? O003 C00B C00F 125.6(3) . . ? N008 C00B C00F 105.1(3) . . ? C00E C00C N008 121.2(4) . . ? C00E C00C C00Q 120.1(4) . . ? C00Q C00C N008 118.7(4) . . ? N00A C00D C00F 112.3(3) . . ? N00A C00D C00T 122.4(4) . . ? C00T C00D C00F 125.2(3) . . ? C00C C00E H00E 120.3 . . ? C00C C00E C00S 119.5(4) . . ? C00S C00E H00E 120.3 . . ? N009 C00F C00B 111.8(3) . . ? N009 C00F C00D 113.6(3) . . ? N009 C00F C00I 112.3(3) . . ? C00B C00F C00I 107.4(3) . . ? C00D C00F C00B 100.4(3) . . ? C00D C00F C00I 110.6(3) . . ? C00K C00G Br01 118.6(3) . . ? C00K C00G C00P 121.8(4) . . ? C00P C00G Br01 119.6(3) . . ? O004 C00H N009 110.5(3) . . ? O006 C00H O004 126.8(4) . . ? O006 C00H N009 122.7(4) . . ? O002 C00I C00F 104.5(3) . . ? O002 C00I C00J 106.3(3) . . ? O002 C00I C00L 111.8(3) . . ? C00J C00I C00F 107.9(3) . . ? C00L C00I C00F 108.3(3) . . ? C00L C00I C00J 117.2(3) . . ? O005 C00J C00I 114.0(3) . . ? O007 C00J O005 124.4(4) . . ? O007 C00J C00I 121.5(4) . . ? C00G C00K H00K 120.7 . . ? C00G C00K C00M 118.5(4) . . ? C00M C00K H00K 120.7 . . ? C00M C00L C00I 118.1(3) . . ? C00N C00L C00I 123.3(3) . . ? C00N C00L C00M 118.3(4) . . ? C00K C00M C00L 121.2(4) . . ? C00K C00M H00M 119.4 . . ? C00L C00M H00M 119.4 . . ? C00L C00N H00N 119.5 . . ? C00L C00N C00P 121.1(4) . . ? C00P C00N H00N 119.5 . . ? C00U C00O C00W 121.5(4) . . ? C00Y C00O C00U 118.5(4) . . ? C00Y C00O C00W 120.0(4) . . ? C00G C00P C00N 119.0(4) . . ? C00G C00P H00P 120.5 . . ? C00N C00P H00P 120.5 . . ? C00C C00Q H00Q 120.3 . . ? C00X C00Q C00C 119.4(4) . . ? C00X C00Q H00Q 120.3 . . ? C00S C00R H00R 120.3 . . ? C00X C00R H00R 120.3 . . ? C00X C00R C00S 119.3(4) . . ? C00E C00S H00S 119.6 . . ? C00R C00S C00E 120.8(4) . . ? C00R C00S H00S 119.6 . . ? C00D C00T H00A 109.5 . . ? C00D C00T H00B 109.5 . . ? C00D C00T H00C 109.5 . . ? H00A C00T H00B 109.5 . . ? H00A C00T H00C 109.5 . . ? H00B C00T H00C 109.5 . . ? C00O C00U H00U 119.8 . . ? C011 C00U C00O 120.4(4) . . ? C011 C00U H00U 119.8 . . ? O004 C00V C012 102.1(3) . . ? O004 C00V C014 110.3(3) . . ? O004 C00V C015 109.8(4) . . ? C014 C00V C012 110.6(4) . . ? C015 C00V C012 110.9(4) . . ? C015 C00V C014 112.6(4) . . ? O002 C00W C00O 107.9(3) . . ? O002 C00W H00D 110.1 . . ? O002 C00W H00F 110.1 . . ? C00O C00W H00D 110.1 . . ? C00O C00W H00F 110.1 . . ? H00D C00W H00F 108.4 . . ? C00Q C00X H00X 119.6 . . ? C00R C00X C00Q 120.8(4) . . ? C00R C00X H00X 119.6 . . ? C00O C00Y H00Y 119.6 . . ? C013 C00Y C00O 120.9(4) . . ? C013 C00Y H00Y 119.6 . . ? C011 C00Z H00Z 119.8 . . ? C011 C00Z C013 120.4(4) . . ? C013 C00Z H00Z 119.8 . . ? O005 C010 H01A 109.5 . . ? O005 C010 H01B 109.5 . . ? O005 C010 H01C 109.5 . . ? H01A C010 H01B 109.5 . . ? H01A C010 H01C 109.5 . . ? H01B C010 H01C 109.5 . . ? C00U C011 H011 120.0 . . ? C00Z C011 C00U 120.1(4) . . ? C00Z C011 H011 120.0 . . ? C00V C012 H01D 109.5 . . ? C00V C012 H01E 109.5 . . ? C00V C012 H01F 109.5 . . ? H01D C012 H01E 109.5 . . ? H01D C012 H01F 109.5 . . ? H01E C012 H01F 109.5 . . ? C00Y C013 H013 120.2 . . ? C00Z C013 C00Y 119.7(4) . . ? C00Z C013 H013 120.2 . . ? C00V C014 H01G 109.5 . . ? C00V C014 H01H 109.5 . . ? C00V C014 H01I 109.5 . . ? H01G C014 H01H 109.5 . . ? H01G C014 H01I 109.5 . . ? H01H C014 H01I 109.5 . . ? C00V C015 H01J 109.5 . . ? C00V C015 H01K 109.5 . . ? C00V C015 H01L 109.5 . . ? H01J C015 H01K 109.5 . . ? H01J C015 H01L 109.5 . . ? H01K C015 H01L 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br01 C00G 1.916(4) . ? O002 C00I 1.420(5) . ? O002 C00W 1.463(4) . ? O003 C00B 1.216(5) . ? O004 C00H 1.339(5) . ? O004 C00V 1.479(5) . ? O005 C00J 1.323(5) . ? O005 C010 1.456(5) . ? O006 C00H 1.215(5) . ? O007 C00J 1.213(5) . ? N008 N00A 1.406(5) . ? N008 C00B 1.371(5) . ? N008 C00C 1.419(5) . ? N009 H009 0.8800 . ? N009 C00F 1.442(5) . ? N009 C00H 1.366(5) . ? N00A C00D 1.289(5) . ? C00B C00F 1.542(5) . ? C00C C00E 1.378(6) . ? C00C C00Q 1.395(6) . ? C00D C00F 1.520(5) . ? C00D C00T 1.475(6) . ? C00E H00E 0.9500 . ? C00E C00S 1.391(6) . ? C00F C00I 1.585(5) . ? C00G C00K 1.370(6) . ? C00G C00P 1.379(6) . ? C00I C00J 1.565(5) . ? C00I C00L 1.538(5) . ? C00K H00K 0.9500 . ? C00K C00M 1.391(6) . ? C00L C00M 1.396(6) . ? C00L C00N 1.386(6) . ? C00M H00M 0.9500 . ? C00N H00N 0.9500 . ? C00N C00P 1.386(6) . ? C00O C00U 1.390(6) . ? C00O C00W 1.494(6) . ? C00O C00Y 1.387(6) . ? C00P H00P 0.9500 . ? C00Q H00Q 0.9500 . ? C00Q C00X 1.389(6) . ? C00R H00R 0.9500 . ? C00R C00S 1.383(6) . ? C00R C00X 1.374(7) . ? C00S H00S 0.9500 . ? C00T H00A 0.9800 . ? C00T H00B 0.9800 . ? C00T H00C 0.9800 . ? C00U H00U 0.9500 . ? C00U C011 1.389(6) . ? C00V C012 1.516(6) . ? C00V C014 1.516(6) . ? C00V C015 1.513(7) . ? C00W H00D 0.9900 . ? C00W H00F 0.9900 . ? C00X H00X 0.9500 . ? C00Y H00Y 0.9500 . ? C00Y C013 1.384(6) . ? C00Z H00Z 0.9500 . ? C00Z C011 1.367(7) . ? C00Z C013 1.380(7) . ? C010 H01A 0.9800 . ? C010 H01B 0.9800 . ? C010 H01C 0.9800 . ? C011 H011 0.9500 . ? C012 H01D 0.9800 . ? C012 H01E 0.9800 . ? C012 H01F 0.9800 . ? C013 H013 0.9500 . ? C014 H01G 0.9800 . ? C014 H01H 0.9800 . ? C014 H01I 0.9800 . ? C015 H01J 0.9800 . ? C015 H01K 0.9800 . ? C015 H01L 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Br01 C00G C00K C00M -175.9(3) . . . . ? Br01 C00G C00P C00N 177.1(3) . . . . ? O002 C00I C00J O005 128.1(3) . . . . ? O002 C00I C00J O007 -48.8(5) . . . . ? O002 C00I C00L C00M 18.7(5) . . . . ? O002 C00I C00L C00N -167.8(3) . . . . ? O003 C00B C00F N009 54.1(5) . . . . ? O003 C00B C00F C00D 174.9(4) . . . . ? O003 C00B C00F C00I -69.5(5) . . . . ? N008 N00A C00D C00F -1.1(4) . . . . ? N008 N00A C00D C00T 174.4(3) . . . . ? N008 C00B C00F N009 -129.0(3) . . . . ? N008 C00B C00F C00D -8.3(4) . . . . ? N008 C00B C00F C00I 107.4(3) . . . . ? N008 C00C C00E C00S -177.5(4) . . . . ? N008 C00C C00Q C00X 178.1(4) . . . . ? N009 C00F C00I O002 62.1(4) . . . . ? N009 C00F C00I C00J -50.8(4) . . . . ? N009 C00F C00I C00L -178.6(3) . . . . ? N00A N008 C00B O003 -174.7(4) . . . . ? N00A N008 C00B C00F 8.6(4) . . . . ? N00A N008 C00C C00E 174.2(3) . . . . ? N00A N008 C00C C00Q -6.3(5) . . . . ? N00A C00D C00F N009 125.3(4) . . . . ? N00A C00D C00F C00B 5.8(4) . . . . ? N00A C00D C00F C00I -107.4(4) . . . . ? C00B N008 N00A C00D -5.1(4) . . . . ? C00B N008 C00C C00E -2.0(6) . . . . ? C00B N008 C00C C00Q 177.5(4) . . . . ? C00B C00F C00I O002 -174.6(3) . . . . ? C00B C00F C00I C00J 72.5(4) . . . . ? C00B C00F C00I C00L -55.3(4) . . . . ? C00C N008 N00A C00D 178.1(3) . . . . ? C00C N008 C00B O003 1.7(7) . . . . ? C00C N008 C00B C00F -175.0(3) . . . . ? C00C C00E C00S C00R -1.6(6) . . . . ? C00C C00Q C00X C00R 0.5(6) . . . . ? C00D C00F C00I O002 -65.9(4) . . . . ? C00D C00F C00I C00J -178.8(3) . . . . ? C00D C00F C00I C00L 53.4(4) . . . . ? C00E C00C C00Q C00X -2.4(6) . . . . ? C00F N009 C00H O004 -168.8(3) . . . . ? C00F N009 C00H O006 11.6(6) . . . . ? C00F C00I C00J O005 -120.2(3) . . . . ? C00F C00I C00J O007 62.8(5) . . . . ? C00F C00I C00L C00M -96.0(4) . . . . ? C00F C00I C00L C00N 77.6(4) . . . . ? C00G C00K C00M C00L -0.9(6) . . . . ? C00H O004 C00V C012 178.3(4) . . . . ? C00H O004 C00V C014 60.7(5) . . . . ? C00H O004 C00V C015 -64.0(5) . . . . ? C00H N009 C00F C00B 47.7(5) . . . . ? C00H N009 C00F C00D -65.1(4) . . . . ? C00H N009 C00F C00I 168.5(3) . . . . ? C00I O002 C00W C00O -168.0(3) . . . . ? C00I C00L C00M C00K 172.6(4) . . . . ? C00I C00L C00N C00P -171.0(4) . . . . ? C00J C00I C00L C00M 141.7(3) . . . . ? C00J C00I C00L C00N -44.8(5) . . . . ? C00K C00G C00P C00N -0.6(6) . . . . ? C00L C00I C00J O005 2.3(5) . . . . ? C00L C00I C00J O007 -174.6(3) . . . . ? C00L C00N C00P C00G -1.6(6) . . . . ? C00M C00L C00N C00P 2.6(6) . . . . ? C00N C00L C00M C00K -1.3(6) . . . . ? C00O C00U C011 C00Z -0.4(6) . . . . ? C00O C00Y C013 C00Z 1.3(7) . . . . ? C00P C00G C00K C00M 1.9(6) . . . . ? C00Q C00C C00E C00S 3.0(6) . . . . ? C00S C00R C00X C00Q 0.9(6) . . . . ? C00T C00D C00F N009 -50.0(5) . . . . ? C00T C00D C00F C00B -169.5(4) . . . . ? C00T C00D C00F C00I 77.2(5) . . . . ? C00U C00O C00W O002 93.5(4) . . . . ? C00U C00O C00Y C013 -0.2(6) . . . . ? C00V O004 C00H O006 0.3(6) . . . . ? C00V O004 C00H N009 -179.3(3) . . . . ? C00W O002 C00I C00F -169.5(3) . . . . ? C00W O002 C00I C00J -55.5(4) . . . . ? C00W O002 C00I C00L 73.6(4) . . . . ? C00W C00O C00U C011 178.5(4) . . . . ? C00W C00O C00Y C013 -178.9(4) . . . . ? C00X C00R C00S C00E -0.4(6) . . . . ? C00Y C00O C00U C011 -0.2(6) . . . . ? C00Y C00O C00W O002 -87.8(4) . . . . ? C010 O005 C00J O007 -0.1(5) . . . . ? C010 O005 C00J C00I -176.9(3) . . . . ? C011 C00Z C013 C00Y -2.0(7) . . . . ? C013 C00Z C011 C00U 1.5(6) . . . . ?